2-(n-butylamino)acetamide | 148306-04-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(n-butylamino)acetamide
• 英文别名: 2-(Butylamino)acetamide
• CAS: 148306-04-1
• 化学式: C₆H₁₄N₂O
• mdl: MFCD09729639
• 分子量: 130.19
• InChiKey: XYIJSPFBTWXBGM-UHFFFAOYSA-N

物化性质

• 沸点：
  247.9±23.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 2-(n-butylamino)acetamide 在 三氯氧磷 、 水 作用下， 以48%的产率得到1-butyl-4-chloro-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  Polyfunctional imidazoles: I. Synthesis of 1-substituted 4-chloro-1H-imidazole-5-carbaldehydes by Vilsmeier-Haack reaction

  摘要：

  2-[Alkyl(aryl)amino]acetamides in reaction with Vilsmeier-Haack reagent afforded 1-alkyl(aryl)-4-chloro-1H-imidazole-5-carbaldehydes.

  DOI：

  10.1134/s1070428009080168
• 作为产物：
  描述：

  聚合甲醛 、 氰化钾 、 正丁胺盐酸盐 在 2-巯基乙醇 作用下， 生成 2-(n-butylamino)acetamide
  参考文献：
  名称：

  Mechanism of inactivation of monoamine oxidase-B by the anticonvulsant agent milacemide (2-(n-pentylamino)acetamide)

  摘要：

  The anticonvulsant agent milacemide (2-(n-pentylamino)acetamide) is known to inactivate monoamine oxidase-B (MAO-B). Various isotopically labeled analogues of milacemide are used to elucidate the mechanism of inactivation of MAO-B by this compound. The metabolites of the oxidation of milacemide by MAO-B (pentanoic acid, pentanal, and glycinamide) are shown not to be responsible for inactivation. MAO was inactivated with 2-(n-pentylamino)-acetamide (1a), 2-(n-pentylamino)[2,2-H-2(2)]acetamide (1b), and 2-([1,1-H-2(2)]-n-pentylamino)acetamide(1c). Compound 1b exhibited little or no isotope effect on inactivation (k(inact)/K(I)) and 1c showed an isotope effect of 4.55 on k(inact)/K(I). These compounds also were found to be excellent substrates for MAO-B; lb showed no isotope effect, but 1c exhibited an isotope effect of 4.53 on k(cat)/K(m). Incubation of MAO with 2-(n-pentylamino)[2-C-14] acetamide followed by dialysis under denaturing conditions resulted in the incorporation of 0.7 equiv of radioactivity per enzyme molecule. The same treatment with 2-([1-C-14]-n-pentylamino)acetamide led to the incorporation of 4 equiv of radioactivity into the enzyme. The excess radioactivity bound presumably arises from the [C-14]pentanal that is generated during turnover. In order to test this, MAO-B was incubated with [1-C-14]pentylamine under similar conditions and 5.9 equiv of radioactivity was incorporated into the denatured enzyme. Therefore, the entire molecule becomes attached to the enzyme during inactivation. By following changes in the flavin absorption spectrum during inactivation with milacemide, it was shown that the flavin becomes reduced; however, denaturation of the inactivation enzyme causes flavin reoxidation under conditions where radioactivity for 2-(n-pentylamino)[2-C-14]acetamide remains bound. This suggests that milacemide is oxidized during inactivation and the adduct results from attachment of milacemide to an amino acid residue, not to the flavin cofactor. Inactivation with 2-(11-C-14]-n-pentylamino)acetamide produced [C-14]pentanoic acid and [C-14]-pentylamine in the ratio of 92:8. Inactivation of MAO with 2-(n-pentylamino)[2-C-14]acetamide gave [C-14]glycinamide and [C-14]oxamic acid, further supporting oxidation reactions at both the pentyl side chain and the acetamido methylene. All of these results indicate that milacemide is oxidized at both the pentyl methylene and the acetamido methylene. Pentyl oxidation leads to inactivation, but it is not clear if acetamido methylene oxidation also leads to inactivation (Scheme I).

  DOI：

  10.1021/ja00065a001

文献信息

• Novel polyamine analogues as therapeutic and diagnostic agents
  申请人：ORIDIGM CORPORATION

  公开号：EP1085011A1

  公开（公告）日：2001-03-21

  Novel inhibitors of polyamine transport having inhibition constants two orders of magnitude lower than those of known compounds are disclosed. These polyamine analogues are useful pharmaceutical agents for treating disease where it is desired to inhibit polyamine transport or other polyamine binding proteins, for example cancer and post-angioplasty injury. Novel chemical synthetic methods to obtain polyamine analogues are disclosed, including the production of a combinatorial polyamine library. These approaches yield analogues with desirable activities both for diagnostic and research assays and therapy. The assays of the invention are useful for high throughput screening of targets in the discovery of drugs that interact with the polyamine system.

  本发明揭示了具有比已知化合物低两个数量级的抑制常数的多胺转运抑制剂。这些多胺类似物是治疗需要抑制多胺转运或其他多胺结合蛋白的疾病的有用药物，例如癌症和血管成形术后的损伤。揭示了获得多胺类似物的新的化学合成方法，包括制备组合多胺库。这些方法产生的类似物具有理想的诊断和研究测定和治疗活性。本发明的测定方法对于高通量筛选与多胺系统相互作用的药物发现目标非常有用。
• Phosphatidylinositol 3-Kinase Inhibitors and Methods of Their Use
  申请人：Bajjalieh William

  公开号：US20100087440A1

  公开（公告）日：2010-04-08

  The present invention comprises small molecule inhibitors of phosphatidylinositol 3-kinase (PI3K), which is associated with a number of malignancies such as ovarian cancer, cervical cancer, breast cancer, colon cancer, rectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases.

  本发明涉及磷脂酰肌醇3-激酶（PI3K）的小分子抑制剂，该酶与多种恶性肿瘤相关，如卵巢癌、宫颈癌、乳腺癌、结肠癌、直肠癌和胶质母细胞瘤等。因此，本发明的化合物可用于治疗、预防和/或抑制这些疾病。
• SUBSTITUTED HETEROARYL- AND ARYL-CYCLOPROPYLAMINE ACETAMIDES AND THEIR USE
  申请人：Ortega Muñoz Alberto

  公开号：US20120264823A1

  公开（公告）日：2012-10-18

  The invention relates to compounds of Formula (I): (A′) x -(A)-(B)—(Z)-(L)-C(═O)NH 2 or pharmaceutically acceptable salts or solvates thereof, wherein: (A) is heteroaryl or aryl; each (A′), if present, is indepedently chosen from aryl, arylalkoxy, arylalkyl, heterocyclyl, aryloxy, halo, alkoxy, haloalkyl, cycloalkyl, haloalkoxy, and cyano, wherein each (A′) is substituted with 0, 1, 2 or 3 substituents independently chosen from halo, haloalkyl, aryl, arylalkoxy, alkyl, alkoxy, cyano, sulfonyl, sulfinyl, and carboxamide; X is 0, 1, 2, or 3; (B) is a cyclopropyl ring, wherein (A) and (Z) are covalently bonded to different carbon atoms of (B); (Z) is —NH—; and (L) is —(CH 2 ) m CR 1 ,R 2 —, wherein m is 0, 1, 2, 3, 4, 5, or 6, and wherein R 1 and R 2 are each independently hydrogen or C 1 -C 6 alkyl; provided that, if (L) is —CH 2 — or —CH(CH 3 )—, then X is not 0. The compounds of the invention are useful in the treatment of diseases such as cancer and neurodegenerative diseases.

  本发明涉及式（I）的化合物：（A'）x-（A）-（B）-（Z）-（L）-C（═O）NH2或其药学上可接受的盐或溶剂，其中：（A）是杂环芳基或芳基；每个（A'）（如果存在）独立地选择自芳基，芳基烷氧基，芳基烷基，杂环芳基，芳氧基，卤素，烷氧基，卤代烷基，环烷基，卤代烷氧基和氰基，其中每个（A'）都被0、1、2或3个取代基独立地取代，所述取代基独立地选择自卤素，卤代烷基，芳基，芳基烷氧基，烷基，烷氧基，氰基，磺酰基，磺酰亚基和羧酰胺；X为0、1、2或3；（B）为环丙基环，其中（A）和（Z）与（B）的不同碳原子共价键合；（Z）为—NH—；（L）为—（CH2）mCR1，R2—，其中m为0、1、2,3,4,5或6，R1和R2各自独立地为氢或C1-C6烷基；但如果（L）为—CH2—或—CH（CH3）—，则X不为0。本发明的化合物在治疗癌症和神经退行性疾病等疾病方面有用。
• Tetracycline Compounds
  申请人：Deng Yonghong

  公开号：US20120208788A1

  公开（公告）日：2012-08-16

  The present invention is directed to a compound represented by Structural Formula (1): or a pharmaceutically acceptable salt thereof. The variables for Structural Formula (I) are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula (I) and its therapeutic use.

  本发明涉及一种由结构式（1）表示的化合物或其药学上可接受的盐。结构式（I）的变量在此定义。本发明还描述了包含结构式（I）化合物的药物组合物及其治疗用途。
• The Quantitative Structure-Herbicidal Activity Relationship of 1-Alkyl-1,3,2-Diazaphospholidin-4-Thione-2-Sulfides
  作者：Liang-Nian He、Ren-Xi Zhuo、Xiao-Peng Liu、Fei Cai

  DOI：10.1080/10426509908546279

  日期：1999.1.1